406-88-2

Upstream product

• 151-67-7 1,1,1-trifluoro-2-bromo-2-chloroethane 
• 109-92-2 ethyl vinyl ether 
• 83706-94-9 1-trifluoromethylprop-1-en-3-ol 
• 25597-16-4 ethyl 4,4,4-trifluorocrotonate 
• 83706-94-9 (E,Z)-4,4,4-trifluoro-2-buten-1-ol 

Downstream Products

• 801289-32-7 (E)-4,4,4-trifluoro-1-phenylbut-2-en-1-ol 
• 94792-96-8 (E)-6,6,6-Trifluoro-1-phenyl-4-hexen-3-ol 

Relevant academic research and scientific papers

Organocatalytic enantioselective Diels-Alder reaction of 4,4,4-trifluorocrotonaldehyde

A highly enantioselective Diels-Alder reaction of 4,4,4-trifluorocrotonaldehyde and dienes was performed with a diarylprolinol silyl ether catalyst. The reaction with cyclopentadiene, 1,3-cyclohexadiene, and 2-substituted 1,3-butadienes yielded the corresponding cycloadducts bearing a trifluoromethylated chiral carbon center with up to 97% ee, whereas the reaction with furan yielded the corresponding Friedel-Crafts adduct with high enantioselectivity.

Sodium dithionite initiated reactions of Halothane with enol ethers: Facile synthesis of 3-trifluoromethyl substituted vinyl carbonyl compounds

A convenient and simple method has been found for the preparation of 5,5,5-trifluoro-3-penten-2-one (3) and 4,4,4-trifluorocrotonaldehyde (9) by a sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to 2-methoxypropene and ethyl vinyl ether, respectively. Reduction of 3 with aluminium isopropoxide afforded allyl alcohol, 5,5,5-trifluoro-3-penten-2-ol (5) and oxidation of 9 gave 4,4,4-trifluorocrotonic acid (11).

Dramatic Effect of γ-Heteroatom Dienolate Substituents on Counterion Assisted Asymmetric Anionic Amino-Cope Reaction Cascades

We report a dramatic effect on product outcomes of the lithium ion enabled amino-Cope-like anionic asymmetric cascade when different γ-dienolate heteroatom substituents are employed. For dienolates with azide, thiomethyl, and trifluoromethylthiol substituents, a Mannich/amino-Cope/cyclization cascade ensues to form chiral cyclohexenone products with two new stereocenters in an anti-relationship. For fluoride-substituted nucleophiles, a Mannich/amino-Cope cascade proceeds to afford chiral acyclic products with two new stereocenters in a syn-relationship. Bromide- and chloride-substituted nucleophiles appear to proceed via the same pathway as the fluoride albeit with the added twist of a 3-exo-trig cyclization to yield chiral cyclopropane products with three stereocenters. When this same class of nucleophiles is substituted with a γ-nitro group, the Mannich-initiated cascade is now diverted to a β-lactam product instead of the amino-Cope pathway. These anionic asymmetric cascades are solvent- and counterion-dependent, with a lithium counterion being essential in combination with etheral solvents such as MTBE and CPME. By altering the geometry of the imine double bond from E to Z, the configurations at the R1 and X stereocenters are flipped. Mechanistic, computational, substituent, and counterion studies suggest that these cascades proceed via a common Mannich-product intermediate, which then proceeds via either a chair (X = N3, SMe, or SCF3) or boat-like (X = F, Cl, or Br) transition state to afford amino-Cope-like products or β-lactam in the case of X = NO2.

The fluorine-containing α, β - production of unsaturated aldehydes

The purpose of the present invention is to provide a fluorine-containing alpha,beta-unsaturated aldehyde, a method for producing same, an optically active fluorine-containing compound using the fluorine-containing alpha,beta-unsaturated aldehyde, and a method for producing same. This method for producing a fluorine-containing alpha,beta-unsaturated aldehyde is a method for producing a fluorine-containing alpha,beta-unsaturated aldehyde represented by formula (1) and comprises: an oxidizing step of oxidizing an alcohol represented by formula (2) in a high-boiling-point solvent, which has a higher boiling point than the corresponding alpha,beta-unsaturated aldehyde, by using an oxidizing agent that is insoluble to the high-boiling-point solvent; and a purifying step of purifying the reaction solution obtained in the oxidizing step by distillation. In formulae (1) and (2), R1 and R2 each independently represent a hydrogen atom or a fluorine atom, and X is 2 or 3.

NO-RELEASING NITROOXY-CHROMENE CONJUGATES

The present invention provides NO-releasing nitrooxy-alkylenyl-linked-chromene conjugates, having the structure of Formula (1) wherein R1, R2, R3, R4, X, and L are as defined in the detailed description; pharmaceutical compositions comprising at least one compound o Formula (I); and methods useful for healing wounds, preventing and treating cancer and treating actinic keratosis, cystic fibrosis, and acne, using a compound of Formula (1).

NO-RELEASING NONOATE(OXYGEN-BOUND)CHROMENE CONJUGATES

The present invention provides NO-releasing NONOate(oxygen bound)chromene conjugates, having the structure of Formula (I): wherein Z, R1, R2, R3, R4, R5, R6, and R7 are as defined in the detailed description; pharmaceutical compositions comprising at least one compound of Formula (I); and methods useful for healing wounds, preventing and treating cancer, or treating actinic keratosis, cystic fibrosis, or acne, using a compound of Formula (I).

NO-RELEASING NITROOXY-CHROMENE CONJUGATES

The present invention provides NO-releasing nitrooxy-alkylenyl-linked-chromene conjugates, having the structure of Formula (1 ) wherein R1, R2, R3, R4, X, and L are as defined in the detailed description; pharmaceutical compositions comprising at least one compound o Formula (I); and methods useful for healing wounds, preventing and treating cancer and treating actinic keratosis, cystic fibrosis, and acne, using a compound of Formula (1).

NO-RELEASING GUANIDINE-CHROMENE CONJUGATES

The present disclosure provides NO-releasing guanidine-chromene conjugates, having the structure of Formula (I): wherein R1, R2, R3, R4, R10, and L are as defined in the detailed description; pharmaceutical compositions comprising at least one of the compounds of Formula (I); and methods useful for healing wounds, preventing and treating cancer, or treating actinic keratosis, cystic fibrosis, acne, or a disease mediated by arginine deficiency using a compound of Formula (I).

Facile one-pot preparation of allylic alcohols with a fluorine-containing alkyl group at the γ-position

A useful one-pot preparation method of allylic alcohols with fluorinated alkyl groups at the γ position was developed from the corresponding enoates by way of the DIBAL-mediated half reduction, followed by nucleophilic attack of Grignard reagents to aldehydes equilibrating with aluminium acetals.

Practical synthesis of 4,4,4-trifluorocrotonaldehyde: A versatile precursor for the enantioselective formation of trifluoromethylated stereogenic centers via organocatalytic 1,4-additions

The practical synthesis of 4,4,4-trifluorocrotonaldehyde (1) and its application to enantioselective 1,4-additions are described. The organocatalytic 1,4-addition of 1 with several nucleophiles such as heteroaromatics, alkylthiols and aldoximes afforded t